75245-14-6Relevant academic research and scientific papers
Sterically Hindered Olefines, VII: Dehydration of Aliphatic Di-tert-butylalkylcarbinols. Force-Field Calculations of Highly Hindered Ethylenes
Lenoir, Dieter,Dauner, Harald,Frank, Robert M.
, p. 2636 - 2647 (2007/10/02)
The tertiary carbinols 1-3 are prepared from the corresponding methyl esters and tert-butyllithium.Dehydration is achieved by treatment with SOCl2 in pyridine and with basic Al2O3.From carbinol 3 the olefine 6 is formed in low yield while 1 and 2 show 1,3-elimination yielding the rearranged olefines 8 and 11, respectively.Methyl 1-methyl-2-adamantanecarboxylate (17) reacts with tert-butyllithium to the ketone 18 exclusively. - Force-field calculations have been performed on a number of highly substituted olefines using Allingers MMI program.For tetra-tert-butylethylene (22) a strain energy of 100.0 kcal/mol and a torsion angle of 45.1 degree is calculated.The geometry of syn-fenchylidenefenchane (27) is calculated and compared with the values determined by x-ray structural analysis.
